Trifluoroacetic acid → HCID 90308925, compound

HRID 2283675Notes

Reaction equation

HRID 2283675 reaction equation
[CH3:1][NH2:2].CO.C(OC([NH:12][C:13]1[C:21]2[CH:20]=[CH:19][S:18][C:17]=2[CH:16]=[C:15]([C:22]([O:24]CC)=O)[CH:14]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:12][C:13]1[C:21]2[CH:20]=[CH:19][S:18][C:17]=2[CH:16]=[C:15]([C:22]([NH:2][CH3:1])=[O:24])[CH:14]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 57454252Monomethylamine methanolHCID 90308894HCID 90308894, compound

Product 1

HCID 90308925HCID 90308925, compound

Conditions

Temperature
90 °C

Procedure

A 40% methylamine-methanol solution (3 ml) was added to ethyl 4-(tert-butoxycarbonylamino)benzo[b]thiophene-6-carboxylate obtained in Example 22 (Step 3) (110 mg), and the reaction solution was stirred at 90° C. overnight. Trifluoroacetic acid (0.5 ml) was added to the resultant residue, and the reaction solution was stirred at room temperature for 15 minutes. Thereafter, the solvent was evaporated under vacuum, and the residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate) to obtain 4-amino-N-methylbenzo[b]thiophene-6-carboxamide.

Workup

  1. stirringthe reaction solution was stirred at room temperature for 15 minutes
  2. customThereafter, the solvent was evaporated under vacuum
  3. customthe residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate)

Sources & evidence

ORD record
ord-02ecc358328347a3a5d47b61fbc5958f
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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